Dave introduces Bill at a Broadcasting Society event after taking speaking lessons from Bill. Matthew learns about gambling from Joe, falling $20,000 into debt.

Jimmy loses Bill in a poker game. Lisa competes in Jimmy's place to win him back. Joe uses a hidden camera inside a Boba Fett action figure to keep up with the action.

Jimmy teaches Beth how to play the stock market, prompting Bill to crash their lessons for some inside information.

Bill weighs the options of joining a health club; Beth fails to exercise restraint after learning a secret about Dave; and Jimmy fears he won't measure up at a dinner party with the Clintons.

Envy rears its ugly head when Lisa is named "Cutest Reporter in New York"; Bill leads a crusade against rap.

Dave gets low marks for honesty after he lets staffers evaluate each other, but fails to mention that Lisa came up with the idea. Meanwhile, Jimmy scores a legal victory with Joe as his lawyer.

Dave unveils a previously hidden talent to compete in a charity talent show. If a WNYX staff member wins, Mr. James will re-hire Matthew.

Mr. James gives Matthew a small toy car. Mr. James urges Dave and Lisa to get back together when a secret study reveals they're more productive when they're a couple.

Lisa is treated like a male by office co-workers, who revert to their boorish selves when all other females are out sick.

Jon Lovitz joins the cast as Max Louis, hired because of a connection to Bill. The idea of "Y2K" wreaks havoc at the office.

It comes out that Max doctored his resume; Lisa goes undercover at a restaurant.

Dave tries to tape a message for students at his alma mater; Lisa tries to cure her speech impediment.

Matthew's 30th birthday causes him to adopt the persona of an 18 year old. Lisa protests Jimmy's plan to build a 200 story skyscraper.